MAGNESIUM SILICATE (synthetic) → N-(1-Methylethyl)-N'-[2-[methyl(phenylmethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea

HRID 4215

Reaction equation

HRID 4215 reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][NH2:5].[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH3:25][CH:26]([NH:28][CH2:29][CH2:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH3:27].[O-][Si]([O-])=O.[Mg+2]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:27][CH:26]([N:28]([CH2:29][CH2:30][S:31]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])=[O:33])[C:13]([NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:14])[CH3:25]

Participants

7

Reactant 4

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 682631,1'-CarbonyldiimidazoleHCID 3014812(2-Aminoethyl)(benzyl)methylamineHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Product 1

HCID 20152874N-(1-Methylethyl)-N'-[2-[methyl(phenylmethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17.90 g (0.045 mole) of N-methyl-N-(phenylmethyl)-1,2-ethanediamine and 1,1'-carbonyldiimidazole (0.05 mole) in 100 ml of tetrahydrofuran was stirred at room temperature for 1 hour. To the mixture was added 10.52 g, (0.04 mole) of 1-methyl-N-[2-(phenysulfonyl)ethyl]ethanamine and the resulting solution heated overnight at gentle reflux. The reaction mixture was stripped to dryness and partitioned between chloroform and water; removal of chloroform gave a dark brown oil. The oil was dissolved in chloroform and extracted with 1N sulfuric acid (saturated with sodium chloride). The acidic layer was made alkaline, extracted with chloroform, and the solvent removed to give a light brown oil. The oil was subjected to chromatography on a Florisil column and eluted with methanol-methylene chloride. After combining appropriate fractions from the column and removing solvent, an oil was obtained. The oil was triturated with diethyl ether and dried at 80° C. in vacuo overnight. This furnished 6.75 g (40.4%) of clear oil.

Workup

  1. temperaturethe resulting solution heated overnight at gentle reflux
  2. custompartitioned between chloroform and water
  3. customremoval of chloroform
  4. customgave a dark brown oil
  5. extractionextracted with 1N sulfuric acid (saturated with sodium chloride)
  6. extractionextracted with chloroform
  7. customthe solvent removed
  8. customto give a light brown oil
  9. washeluted with methanol-methylene chloride
  10. customremoving solvent
  11. customan oil was obtained
  12. customThe oil was triturated with diethyl ether
  13. customdried at 80° C. in vacuo overnight

Sources & evidence

ORD record
ord-082c10047ad64187a1aa3f32d4231702
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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